O’Keefe began his backpacking journey of nearly 2,200 miles in Georgia in February, hoping to finish in late May. He was forced to hike and snowshoe through heavy snow and had to leave the trail temporarily in April with shin splints. This summer, he left the trail to take a class at the U.S. Naval Academy, where he will resume classes later this summer.

Carrying a base pack that weighs only eight pounds, including his sleeping bag but excluding food, O’Keefe hopes to average about 26 miles a day through the mountains of New England, reaching the northern part of the Appalachian Trail — Mount Katahdin, Maine — Aug. 9 or 10.